Diamond Head Oahu

Oahu Vacation Packages

 
Oahu, "The Gathering Place", is home to Honolulu, Hawaii's largest city. Iconic Waikiki dazzles with its classic beaches, exciting nightlife and world-class cusine. On the northen side of the island, the surfer's paradise of North Shore, home of the Banzi pipeline and scenic rainforests offers a laid back island style visitors are sure to enjoy. To the West, Pearl Harbor is steeped in history with its WWII memorials and massive ships. Throughout the island a fusion of asian, polynesian and western culture give Oahu a flavor all its own. Enjoy the best Oahu deals on Hawaii vacation packages today!

Hawaii Travel & Testing Guidelines

In order to avoid a mandatory 14-day quarantine, travelers to Hawaii must take a COVID-19 test within 72 hours of the final leg of their flight to Hawaii and receive proof of a negative test result prior to boarding. Travelers must complete the State of Hawaii's Safe Travels online travel and health questionnaire and upload proof or a negative COVID-19 test result within 24 hours of flight departure to Hawaii. The test must be an FDA-approved NAAT COVID-19 test taken at an approved testing facility. Children ages 4 years and under are not required to provide a pre-travel test when traveling with parents. For travel between the Hawaiian Islands, another COVID-19 test may be required within 72-hours of arrival to bypass quarantine. Interisland passengers arriving on Oahu are not required to quarantine.  More information on each island's testing requirements is available here. Testing requirements are subject to change. Gov. David Ige has extended the statewide mask mandate, which requires all persons in the State to wear a face covering over their nose and mouth when in public.

Pleasant Holidays has partnered with CVS Health, a trusted testing partner approved by the state of Hawaii to provide travelers to Hawaii with options for pre-travel COVID-19 testing at 2,800 locations across the continental U.S. Learn more and make your appointment here.

CVS

Happy Hawaii Holidays
Give the gift of travel this holiday season with discounts and extras

  • Book by 1/10/21 for travel through 6/30/21
All Deals Include: Round-trip flights, hotel accommodations, taxes and more
  • Waikiki, Oahu Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.

    With breathtaking views of iconic Diamond Head and steps to Waikiki Beach, experience Aloha Spirit with daily activities, regional cuisine and live entertainment at this lively hotel with an urban-Hawaiian vibe.

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  • Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Lush grounds, six spectacular pools, a beachfront lagoon, waterfalls and an array of shops and restaurants are all part of the "Village" experience at this expansive resort.

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  • Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This legendary resort, "The First Lady of Waikiki," combines turn-of the-century Victorian elegance with modern Westin amenities and luxuries.

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  • Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    “Where the Beach Comes Alive” Our extended ohana (family) will discover local beach and surf culture at this hotel on Waikiki Beach.

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  • Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    "Sharing the Arts & Culture of Hawaii" This distinctive, refined hotel presents a new vision of hospitality, combining timeless traditions with modern elegance.

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  • Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Located on the best stretch of Waikiki beach, this trendy, sophisticated resort ushers in a new level of style to the Waikiki scene.

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  • Waikiki, Oahu Our 3.5-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Experience comfort and relaxation in the heart of Waikiki at this hotel while enjoying an exceptional vacation value.

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  • Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Explore the excitement of Oahu in one of Hawaii’s most fashionable zip codes. Just steps from renowned warm waters and spectacular views.

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  • Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This hotel featuring 1 & 2-bedroom suites offers spacious and comfortable accommodations just a short walk from Waikiki Beach. Free daily breakfast included.

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  • Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Named among the Best Resorts in Hawaii in the 2019 Condé Nast Readers' Choice Awards, This newly renovated family-friendly resort is across from Waikiki Beach within easy walking to nearby shops, restaurants, and attractions.

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  • Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This landmark resort offers some of the best views in Waikiki. Spacious rooms reflect the colors and ambiance that is uniquely Hawaii.

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  • Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    "An Oasis in the Heart of Waikiki" This brand new lifestyle resort which just completed a $35 million modernization offers contemporary comfort, camaraderie and fun.

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  • Waikiki, Oahu Our 5-Star classification designates those select properties that provide exquisite service and amenities. The discriminating traveler will find the accommodations, ambiance, dining, and staff assistance of the highest caliber. These properties offer the utmost in luxury and will provide an outstanding experience.

    This legendary hotel, known as the Pink Palace of the Pacific, offers a redefined luxury experience.

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  • Waikiki, Oahu Our 3-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort.

    Discover exceptional value at this family-friendly hotel offering 1- and 2-bedroom suites with kitchenettes in the heart of Waikiki, just five minutes from the beach.

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  • Waikiki, Oahu Our 3.5-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This boutique condo with 1- and 2-bedroom units with full kitchens and large balconies, brings fresh contemporary style and understated chic to the heart of Waikiki.

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  • Waikiki, Oahu Our 5-Star classification designates those select properties that provide exquisite service and amenities. The discriminating traveler will find the accommodations, ambiance, dining, and staff assistance of the highest caliber. These properties offer the utmost in luxury and will provide an outstanding experience.

    Discover a distinctive resort experience with stylishly-appointed studios, 3- and 4-bedroom suites offering ocean views and five star resort amenities.

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  • Waikiki, Oahu Our 3.5-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This intimate boutique hotel is set at the gateway to Waikiki, just a short walk from the beach, and offers suites and tastefully appointed rooms.

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  • Waikiki, Oahu Our 3-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort.

    This upgraded hotel is conveniently located on Kuhio Avenue, just a short stroll to many of Waikiki's most popular attractions.

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Hawaii $100 OFF per booking: Happy Hawaii Holidays: Valid on new bookings made 11/2/20 - 1/10/21 for select travel through 6/30/21. Minimum 3-night hotel accommodations at participating property and roundtrip airfare required. 
Rates quoted are per person, based on double occupancy unless otherwise stated. Rates for other travel dates may vary. Rates, terms, conditions and itinerary are subject to availability. Certain restrictions apply. Rates shown include government-imposed fees and taxes. Airline fees for optional services, including, but not limited to, baggage fees, may apply. Airline tickets are non-refundable and subject to airline change/cancellation penalties and rules, including pre-flight notification deadlines. Fees and policies vary among airlines and are subject to change without notice. Please contact the airline directly for details and answers to specific questions you may have. Additional restrictions apply. Advertised rates do not include any applicable daily resort or facility fees payable directly to the hotel operator at check-out; such fee amounts will be advised at the time of booking. Where applicable, kids stay free in same room as adults using existing bedding. Occupancy limits apply. Where applicable, kids eat free with full paying adult. Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]